Semiconducting conjugated polymers hold tremendous promise as active layers for transformative electronic devices. This materials class benefits from the structural variety provided by organic chemistry such that highly tunable band structures are attainable for as-synthesized polymers. This dissertation describes the synthesis and characterization of novel imidazole-containing conjugated polymers for the purposes of (de)protonating the as-synthesized materials gaining conjugated poly(ionomer)s. (De)protonation easily enables band structure modification through manipulation of the materials’ ionization potential and electron affinity. Controlled exposure to acids and bases led to reversible (de)protonation observable via UV-visible and photoluminescence spectroscopies. (De)protonation’s effects on polymeric band structures was empirically and computationally examined. Additionally, we scrutinize different approaches for gaining end-functionalized conjugated polymers from AA/BB-type polycondensations and delineate requirements to obtain well-defined chain-ends.